Naturally occurring quinones have attracted considerable interest due to their widespread occurrence, structural diversity and often potent biological activities. The research outlined in this thesis involves the development of synthetic approaches to two novel naphthoquinone derivatives, both of which were discovered during investigations into the bioactive constituents of tropical plant species. Chapter 1 introduces the family of quinonoid compounds and also considers the important role that natural product synthesis can play in structural confirmation and in providing an adequate supply of compounds for further research. Chapter 2 describes the synthesis of elecanacin 36, an unusual cyclobuta-fused naphthalene-1,4-dione derivative which has been isolated from the bulbs of the iris Eleutherine americana Merr. et Heyne (Iridaceae), along with the isomeric and well-known pyranonaphthoquinones eleutherin 38 and isoeleutherin 39. Chapter 3 focuses on an approach to 3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]furan-5,10-dione 37, which has been isolated from the wood of the tropical tree Crescentia cujete L. (Bignoniaceae) and incorporates a rare fully aromatic furofuran moiety.
|Qualification||Doctor of Philosophy|
|Publication status||Unpublished - 2008|